Looking for the best trails around Chappaqua?

Explore the best rated trails in Chappaqua, NY, whether you're looking for an easy walking trail or a bike trail like the South County Trailway and Old Croton Aqueduct Trail . With more than 111 trails covering 832 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Heritage Trail (NY)

well maintained , interesting sites, and views along the way.

October, 2025 by toddburrparts

I rode from Harriman to the edge of Goshen. Nice smooth, pavement with little or no bumps. I found some interesting sites and information along the way. I will return to ride the second half of this heritage Trail.

Farmington Canal Heritage Trail

ok

October, 2025 by deceived

Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.

O&W Rail Trail (Ulster County)

O&W Kingston - Kerhonkson

September, 2025 by kaiser

.With a mix of cinders , gravel , dirt & pavement this makes for a nice interesting ride . Along the way in High Falls make a left and visit the D+H canal museum its about a mile down the road . Once you venture a mile and half through a grass area the trail stops however pedal straight out on to Lucas tpk & make left onto 209 then left on main & right on scenic you will then pick up the trail to accord

Accordion

Sullivan O&W Rail Trail

O&W mountaindale - ferndale

September, 2025 by kaiser

Nice scenic ride . The mountaindale side goes through several abandon like towns nice ride mostly dirt / cinders / crushed stone lots of nice scenery for about 3 miles then you end at the Neversink River where a bridge is out so you have to pedal 7 miles via road to hook up on the Fallsburg side which is paved ,nice trail for 4 miles . Would do again , tables , benches and bike tool areas . No road bike for gravel part

Pompton Valley Rail Trail

beautiful new trail

September, 2025 by krawiec.monica

Awesome trail, I tried inline skating and I wouldn’t recommend. It’s definitely possible but not enjoyable. I feel like everything else is doable.

Jones Point Path

Bad shape currently!

September, 2025 by bsmith4_tl

Took a ride on this once nice restored short trail yesterday. The state needs to get back in there and do some basic maintenance. The overgrowth of weeds has turned this into barely a single track lane. Many limbs and broken fencing. It's a shame after all the time and money put into it a few years ago.

Old Croton Aqueduct Trail

OCA south end

September, 2025 by kaiser

Interesting ride did it on a hybrid not a bad ride . Rode from Tarrytown to the end south a few places to get a bite and drink however did not see any porta John’s . Some old stone houses , walls some views of the Hudson River a must see Untermyer park & garden area .

Sandy Hook Multi-Use Pathway

Amazing

September, 2025 by mpd45

Such beautiful bike path going next to shore through wood like settings into old army base around island. Very safe scenic and smooth ride our new favorite place to go.

Farmington Canal Heritage Trail

Rode the entire trail…

September, 2025 by willipar

Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!

Saddle River County Park Bike Path

Heads up that ALL e- bikes are now banned in ALL Bergen County parks. Speed limit of 10mph for all (remaining) vehicles. ¿¿ Bummer.

August, 2025 by acahilly

Heads up that ALL e- bikes are now banned in ALL Bergen County parks. Speed limit of 10mph for all (remaining) vehicles. ¿¿ Bummer.

Walkway Over The Hudson

Walkway Courtesy

August, 2025 by wayne7532

Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.

Sussex Branch Trail

diverse & well maintained

August, 2025 by kjfhall61

The trail is ~ 20 miles in each direction. A good mix of paved, gravel, dirt — with minor sections that are “single track”’ish.

Find Nearby City trails

Accordion

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